The Trouble with Henry

It was the last four-day break before his high school graduation, and Henry was looking forward to spending the Memorial Day weekend up at the lake cabin. His older sister Debra, and her college friend, Miko, would undoubtedly be there too, but Henry wasn't worried. This time their parents would be there to protect him. Of course they had no idea of the abuses Henry suffered under the girls' care during spring break, and they never would know. The photos Debra used to blackmail Henry were an ironclad guarantee that he'd keep his mouth shut. Nevertheless, Henry figured he'd be safe at least this time. What he hadn't counted on was a nasty little virus.

It wasn't a human borne virus, but a computer virus called "B-Bugger." An advanced variant of the "A-Bugger" Trojan-horse virus , it had slipped in through an email attachment and virtually wiped out the server at his family's small business. Henry's father would have to spend the entire holiday weekend restoring the server and rebuilding the database from woefully out-of-date backup files. To make matters worse, Henry's mother volunteered to stay and help him. As soon as Henry realized he'd be alone with his sister and Miko at the cabin again, he tried to back out.

"Why, Henry," his mother exclaimed, "I can't imagine why you wouldn't want to give up an entire weekend at the lake. You've been looking forward to it. Your summer job starts right after graduation, so this is your last chance for a break. You really should go."

His sister, Debra, walked into the room and stood behind their mother. "Yes, Henry. You really must go." She held up her hands and mimed taking a snapshot. Henry was the only one who saw it, and the meaning was all too clear: Come to the cabin, Henry, or those photos I have of you masturbating in my frilly underwear will be all over town. Probably on the internet, too.

Their mother turned and smiled at Debra. "You girls won't mind having him along with just the two of you, do you?"

"Oh, not at all Mother," Debra replied. "Henry is never much trouble." She smiled innocently. "And Miko just adores him."

"Well, then it's settled. Henry, you're going up to the lake with your sister and Miko. I won't have you moping around here while your father and I are trying to work. You'll just be in the way. Now go pack your things."

Henry strode off to his room, fuming. Debra had played the blackmail card again and there was nothing he could do about it. The only question now was how far the girls would go this time. He wouldn't have to wait long to find out.

The next morning Debra and Miko loaded the car while Henry sulked in his room His prayers for bad weather had gone unanswered. He was under no illusions about what was in store for him up at the lake. It would be a very long weekend.

"Henry!" Debra, hollered from downstairs. "Let's go!"

Henry sighed and picked up his small overnight bag. He trudged downstairs, hugged his mother goodbye, and went outside. Debra was already in the driver's seat of the Volvo. Miko held the rear door open and gestured for Henry to get in. To his surprise Miko got in back too, instead of riding up front with Debra. He felt like he'd just been arrested, and Miko was the cop.

Debra turned at the light, and instead of getting on the freeway, she headed across town. Henry looked around curiously, wondering what she had up her sleeve now.

"Uh, Debra?" he asked, "Why are we going this way?"

"Why, to pick up Becky, silly. Didn't I tell you she was coming along?"

In fact, Debra hadn't, and Henry had no doubt she'd also 'forgotten' to mention it to their parents. Henry shuddered. Becky had been in Debra's senior class at high school, but instead of going on to college, she had run into a little trouble with the law. Henry didn't know all the details, but he knew that Becky was what people commonly referred to as a 'bad seed.' Now she was going to join a party in which Henry would undoubtedly be the main attraction.

At that point Henry actually considered jumping from the car and making his escape, but Miko was obviously reading his thoughts. Whenever the car stopped or slowed she tightened her grip on Henry's arm. At one point she pulled his hand down into her lap and shoved it up under her short skirt.

Henry gasped as his fingers touched the damp crotch of her thin cotton panties. He could feel the heat of her sex, and he instantly felt his own cock begin to stir.

Miko looked defiantly into his eyes and kept his hand pressed between her thighs. At last she pulled it free and then rubbed it under Henry's nose so that he could smell her arousal. Then, to Henry's embarrassment, she placed her hand in his lap and gave his erect cock a squeeze.

They pulled into the driveway of a small suburban house and Debra killed the engine. As they got out, the front door opened and Becky came out carrying a large backpack. She was a big girl, a bit on the plump side but not overly so, and she had the muscle tone of a weight-lifter. Debra grabbed her backpack and loaded it into the trunk while Becky exchanged greetings with Miko and then Henry.

"Why Henry!" Becky squealed, "I haven't seen you since you were a little boy! Oh, but look, you're still just a boy. How old are you now?"

"Eighteen," Henry replied sullenly.

"Well you don't look a day over fifteen!"

Henry cringed as Becky pulled him in against her oversized breasts and gave him a crushing hug. Becky's friendly greeting did not dispel Henry's fears. He knew that she could be even crueler than his sister or Miko, and now, alone for the weekend with all three girls, he smelled trouble brewing.

Becky climbed into the front seat with Debra and Miko got in the back beside Henry again. As they pulled out of the driveway, Miko began cuddling him like a stuffed toy, and Henry gave up all thoughts of escape. He suffered Miko's affections in silence, knowing they were nothing compared to whatever else the girls had in store for him.

Miko, sensing Henry's surrender, slid her hand over and unbuttoned his shirt. She fondled his breasts and tweaked his nipples until they were hard. Her other hand dropped down and deftly unzipped his trousers. Henry expected her to reach in and grab his cock next, but Miko had other ideas. She started pulling his pants down.

"Wh-what are you doing?" Henry protested.

"We have to dress you for the trip, Henry." Miko laughed. "Now lift your bottom so I can get rid of these awful boy clothes."

"No, please! You aren't going to make me wear girly stuff again, are you?"

"Of course we are, silly!" Miko laughed. "And if you don't play along, then we'll just have to spank you."

Debra looked up in the rearview mirror and glared at Henry, "And don't forget the photos, little brother."

Shit. It always came down to that; Debra's growing collection of very explicit photos showing Henry wearing her lingerie, masturbating, even humping himself with a candle. He'd be ruined if Debra ever let those pictures out on the street. Henry stopped struggling and allowed Miko to remove his trousers. His shirt came off next, and he was left shivering in nothing but his briefs. Becky handed Miko a sack across the back of the seat. Miko took a small training bra out and held it up to Henry's chest.

"Oh, this will be so cute on you!" Miko exclaimed.

Miko pinched Henry's nipple again, then leaned over and sucked on the other one. After a moment she straightened up and admired the results. Henry's nipples stuck out in little hard, pink points. The other two girls turned to look and laughed out loud. Henry turned beet red, but held his tongue.

Miko fastened the brassiere around Henry's small chest and then reached in the bag again. This time she pulled out a make-up kit. Henry groaned as he saw her flip it open.

She leaned over against the door, spread her legs out and pulled Henry's backside up against her. By wrapping her arms around him and placing her cheek against his, she was able to use her battery-lit compact mirror to illuminate his face and put on his make-up. Henry suffered this indignity in silence, concentrating instead on the feel of her warm crotch grinding against the base of his spine.

He had seen her pussy earlier that spring, when she'd peed on him in the bathtub, and afterward she had forced him to suckle on her little pink clit. The memory of that day caused his penis to stir, and a drop of precum seeped out to stain the front of his briefs.

Miko finished his makeup and pulled a little dress out of the bag. She held it up and Henry obediently raised his arms so she could put it on him. Her hands were all over him as she fussed and arranged the garment into place.

Eventually they reached narrow road leading up to the lake, and a few minutes later turned in and parked by the cabin. Debra built a fire in the large stone fireplace while the others quickly unpacked the car. Henry's awkward attempts to move around in the tight little dress drew gales of laughter from the girls.

"Now isn't this cozy," Debra said, closing the door as Beck brought the last of their luggage inside. "You all want to get comfortable while I get us something to drink?"

Henry started to sit down in the overstuffed armchair but was stopped by his sister's hand on his shirt collar.

"Not so fast, sissy," Debra steered him toward the couch.

Henry found himself seated tightly between Miko and Becky. Miko put her hand on his knee and Becky laid her arm around his shoulder. It was almost like they were all just school chums ... Almost.

Debra brought in some cold beers and passed them out. She even handed one to Henry. Surprised, he eagerly gulped it down, almost choking on it.

"Take it easy young lady," Debra laughed, "You don't have to drink it all at once."

Henry had gotten used to Debra talking to him as if he were a girl. He suspected that it was just her way of making him feel small and weak. At any rate he was so slightly built that she could easily beat the crap out of him, so there wasn't any use in arguing. Besides, there was still the issue of the photos. Henry would remain under her power until Debra decided otherwise and that was that.

The girls talked about school and the boys they knew, while Henry sat drinking his beer, relieved that for the moment at least he been forgotten. He was well into his second bottle and getting a bit light-headed when he felt Miko's hand creep up his thigh and slip under the edge of his dress. Henry felt himself growing erect as she began playing with the small bulge in his briefs.

"Whacha' got there Miko?" Debra asked.

"Little sissy penis," Miko laughed. She ran her hand lower and grabbed Henry's testicles, squeezing them until he yelped. "And baby balls."

"How fun! Why don't you show us?"

"Here, let me help," said Becky.

She and Miko got up and pulled Henry to his feet. They led him into the middle of the room. He stood there, wobbling from the effects of the alcohol while Debra gripped his arm firmly. His head was buzzing and he was only vaguely aware of Miko's fingers unbuttoning his dress. Moments later the dress lay in a heap around his ankles.

"Well, will you look at that," Becky gasped in mock surprise. She pointed at the bulge of Henry's erection pressing out against his cotton briefs. "The little sissy does have something in there!"

Miko unfastened Henry's training bra, removed it, and playfully twisted his nipples. Meanwhile, Becky slid her hand under his waistband and squeezed one of his butt-cheeks. Debra got up and stood in front of Henry, surveying him as if he were a piece of meat.

"Okay Henry, here's how this works. We tell you what to do and you do it. You can imagine what will happen if you don't; trust me, it won't be fun. We have some great photos your friends would love to see. And tonight we'll add a few more to our little 'family album.'"

Henry squirmed nervously as he thought about the pictures of him masturbating and wearing girl's underwear. The fact that he had been trapped and forced into some of the poses would not matter to his school chums. He'd be branded forever as a sissy or queer and his friends would quickly become his tormentors. His sister allowed him to consider this for a moment before continuing.

"Now Henry, we all know what a little sissy-girl you are, so let's start by getting rid of those nasty little boy underpants."

He hesitated ... Debra moved in close and placed her hand on his shoulder.

"You're trembling Henry. Are you afraid?"

Henry nodded.

"You look like you're ready to pee your pants."

Debra looked over at Becky and Miko, and they reached some sort of silent agreement. She turned back to Henry and looked at him evenly, hands on her hips.

"Okay Henry. You can leave them on. In fact you can just stand right there and pee in them while we watch. Go ahead – we've got all night."

Henry was shocked. He knew they were serious. Fifteen minutes passed while he tried to keep from peeing. It was hard now to think of anything else. He was really feeling those two beers he drank.

Debra went into the kitchen and returned with a large bowl. She held it out in front of Henry.

"Put your hands in here," Debra ordered.

Henry placed his hands in the warm water. His overstretched bladder responded almost instantly. A damp spot appeared on the front of his briefs, then rapidly widened until the entire front of the garment was soaked. Small rivulets of pee began running down his legs.

Debra laid the bowl on the floor and forced Henry to squat down over it. There was no stopping it now. The girls all laughed and pointed as pee gushed out of his soaked briefs and splashed into the bowl. There was a flash, and Henry looked up to see Debra holding a camera.

As the last dribbles of pee fell into the bowl, Becky grabbed Henry's, twisted it painfully, and used it to pull him upright.

"That's disgusting Henry! Take them off now, you little shit!"

Henry pulled his wet underpants down to his ankles and stood there completely naked and humiliated. His pale thighs glistened with moisture and a drop of pee hung from his half erect penis. Debra and Miko sat down on the couch, sipped their beers, and smiled at Henry's discomfort. Becky was in charge now and she intended to make a show of it.

"Now take them into the bathroom and put them in the tub." Becky pointed down the hallway.

Henry bent and started to pick up his wet underpants. Whack! He was almost knocked over by a hard slap on his bare ass.

"Not that way!" Becky shouted. "Like a dog!"

Henry hesitated while he tried to understand she meant. Whack! She hit his ass again, shoving his head down with her other hand until he was on his hands and knees.

"That's it," she said, "Now pick it up with your teeth."

Henry leaned down, his tears splattering onto the soiled briefs. With the acrid smell of his urine filling his nostrils he opened his mouth and gripped a corner of the material in his teeth. As he started to get up Becky placed a vicious kick in the crack of his ass, sending him sprawling face-forward onto the carpet. He cried out in pain but managed to keep from losing his grip on the underpants.

"Don't get up!" she shouted, "Crawl into the bathroom with your nasty wet panties and drop them in the bathtub. Then come back here."

Another flashbulb popped in his face as Henry crawled off with the wet underpants gripped in his teeth. After he had deposited his underpants in the tub he crawled back up the hallway towards the sounds girlish laughter.

"Get up!" Becky commanded.

Henry stood and covered his penis with his hands. Becky went into another room and emerged moments later emerged with what appeared to be lingerie. She also held a few other items that Henry recognized as Debra's "toys."

Becky dropped the pile on the couch between Debra and Miko and they all began pawing through the items. Debra held up a tiny g-string for him to see.

"Look Henry! Your favorite color—red! Now aren't these more fun than your stupid old underpants?"

"We'll have him model everything," Becky said, clearly relishing her new role as master of ceremonies, "But first we need to clean him up. For some strange reason he smells like piss."

The girls all laughed, then got up and dragged the hapless Henry down the hall and into the bathroom. They threw him unceremoniously into the tub. Miko whispered something to the other two girls and there was a chorus of giggles. She reached up under her skirt and pulled down her panties, and then hung them on the towel rack. Henry had watched Miko do that once before, so he had a pretty good idea what she might do next. He was right.

Miko climbed into the tub and squatted over Henry. He stole a quick glimpse of her soft dark vagina then squeezed his eyes shut. Seconds later Miko flooded his face with a torrent of hot pee. It soaked his hair, ran down his neck and onto his scrawny chest, and pooled beneath him, warming the cold porcelain tub. She forced out a few final dribbles and then sat down on the edge of the tub facing him.

"Okay," Miko said. "Lick."

Henry opened his eyes and that Miko was holding her dripping foot in front of his face.

"Lick it clean, girlie."

Henry wrinkled his nose at the smell of her pee and forced himself to lick the pee from her foot. She made him clean the other one then got up and pulled her panties back on. Meanwhile Becky had pulled her pants down turned so her wide bottom faced Henry. With the other girls supporting her arms, she hung her bottom way out over the edge of the tub and peed all over Henry. Obviously she had been drinking before they arrived and it took awhile for her to unload the considerable amount of fluid she had saved for poor Henry.

Finally it was Debra's turn and she made the most of it. By positioning her bare bottom over the tub and leaning forward a little she was able to splatter piss over every part of Henry's bare body. She even stopped at one point and shifted up to make certain his head was soaked thoroughly. In spite of himself, Henry couldn't help peeking up at the exposed vaginas during the whole ordeal. His eyes were stinging mightily by the time it was over.

They turned the shower on him and rinsed the pee away, then made him wash out his underpants and hang them up. He was made to stand still with his legs spread apart while the girls scrubbed and probed every part of his body. Finally they rinsed him off and Henry thought the worst was over.

"Lay down here on the bath-mat Henry," he heard his sister say from behind him as her hands guided him onto the floor. "Lay on your side and pull your legs up, like this. That's it. Now don't struggle, we're just going to clean up the rest of you."

Henry looked up to see Becky holding a large red rubber bag with a hose attached. Debra held the other end of the hose which had some type of nozzle attached to it. He saw Miko kneeling down near his legs, then felt her long fingers prying his buttocks apart. Debra placed the cold greasy tip of the nozzle against his puckered hole and pushed. He yelped in pain.

"Relax Henry," Debra said, "or it will hurt more. Just breathe in gently."

Henry drew a breath and tried to relax. Debra suddenly jammed the nozzle inward, burying it all the way to the hilt in his bottom. She released the valve, and Henry felt a warm liquid fullness invade his bowels.

"That's it little brother. Let's get you all filled up, then flushed out."

The bag seemed to take forever to empty. Soon Henry was feeling cramps and he groaned in protest. Debra reached over and rubbed his stomach with her free hand. He was moaning and sobbing when finally they stopped and pulled out the nozzle. The girls helped him up and placed him on the toilet. He did not need their prompting to know what was next. With a loud splash he emptied his bowels, gasping in relief as the pressure was released. Then he heard the water running and looked up to see the bag being refilled.